Don’t Make These Five Dating Mistakes

Mar 14, 2016

Looking back on my dating life, there are some mistakes I made which prevented me from meeting more qualified people to date. This is a personal list, so these won’t apply to everyone, but I hope you’ll find something helpful here. If I could go back in time, I’d fix these top five dating mistakes of mine.



1. Not Having a Wingman When Going Out to Meet New People

It’s only later in life when I realized the importance of having a wingman (or wing-woman) when trying to meet new people. A wingman is so critical to provide motivation, keep you in a good mood, and keep the conversation going with new people that you’ve met (who usually are in groups). Plus, being with a friend makes you appear way less creepy when you’re approaching strangers. Make sure your wing-person understands why you’re out and how to help you meet people!

Women usually go out in groups so they don’t have this problem, however, they often end up being “closed off” in tight circles of conversation which are nearly impenetrable. That’s great f you don’t want anyone else to talk to you. But, if you want to meet new people, don’t be so focused on each other all night. Break up from time to time. Go to the restroom separately. This will make it much less intimidating for guys to meet you.

2. Not Cultivating My Social Circles

What does this mean? My approach to dating was to be really “focused” on women that I was interested in. That’s totally wrong. It’s important to have a large network of friends of both genders and all ages. These friends can be wingmen/wingwomen, they can invite you to parties or other social events, or you may meet one of their friends who you want to date. Having a good network of friends is really important if you want to meet quality people, especially if you’re not into meeting people in clubs and bars all of the time.

3. Wasting Time on Dead-End Relationships

This takes on two forms. The first is wasting time on people who are not interested in you. I’ve done this a lot. I should have been more direct and just asked them out. Even if I had gotten shot down, at least I could move on with my life and spend my time and energy on someone who was actually interested in me!

The second form is spending too much in a relationship where you know you’re not a good match. I’ve done this too. Breaking up is painful and permanent, so once you’re in a relationship, it might seem best to try to fix it, even if you know deep down it’s not going to work. It takes a lot of courage and pain to end a relationship, but if you know it won’t work, you need to be honest with yourself and your partner. You’re not doing yourself or them any favors by sticking around when you know it won’t work.


4. Not Taking Enough Risks

I’m a pretty risk-averse person, not a thrill-seeker at all. But, dating is all about taking risks. A high-quality person won’t just land in your lap (the possible except is Internet dating, but I never had much success with that).

Talking to a stranger that you’re interested can be downright scary, but really, you have nothing to lose and everything to gain!

Just before I was moving out of town, I threw caution to the wind and started asking out all of the women I was interested in. The first one shot me down. But the second one didn’t, and we dated for a year (long distance for most of the time). What if I had had this gung-ho attitude more often?

5. Not Getting Help with Clothes

This one is really embarrassing. I hate shopping for clothes. As a result, I did it as infrequently as possible, and as quickly as possible. I also hate asking for help, so I’d grab something off the rack and get out of the store as soon as I could. But later, a girlfriend of mine pointed out that a lot of my clothes were too big for me. Check out this shirt which I actually used to wear:

Oversize shirt

Compare this to something that actually fits:

Shirt that fits

The moral of the story is to get help from salespeople when shopping for clothes. Or even better, bring a friend along. I wish I had brought one of my female friends to help me – that would have made all of the difference! Plus, maybe it could turn have turned into a date!



I hope my mistakes will help you in your dating life to meet that special someone. What are some of your biggest dating mistakes? Please comment below! – Brian

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